CN106083809A

CN106083809A - Compound, the organic luminescent device including this compound and display device

Info

Publication number: CN106083809A
Application number: CN201610274823.2A
Authority: CN
Inventors: 韩相铉; 金秀娟; 金荣国; 黄皙焕
Original assignee: Samsung Display Co Ltd
Current assignee: Samsung Display Co Ltd
Priority date: 2015-04-28
Filing date: 2016-04-28
Publication date: 2016-11-09
Anticipated expiration: 2036-04-28
Also published as: TW201704223A; KR20160128507A; TWI702209B; US20160322577A1; KR102456078B1; CN106083809B

Abstract

Disclose a kind of compound, a kind of organic luminescent device including this compound and a kind of display device represented by formula 1, wherein, the detailed description of this specification provides the description of formula 1.The organic layer of organic luminescent device can include the compound represented by formula 1.The compound represented by formula 1 can be included in the emission layer of organic layer.Formula 1

Description

Compound, organic light emitting device including the same, and display apparatus including the same

This application claims priority and benefit from korean patent application No. 10-2015-0059635, filed on korean intellectual property office at 28.4.2015, the entire contents of which are incorporated herein by reference.

Technical Field

One or more example embodiments relate to a compound and an organic light emitting device including the same.

Background

Organic Light Emitting Devices (OLEDs) are self-emitting devices with wide viewing angles, high contrast, and short response times. OLEDs also exhibit excellent brightness, drive voltage, and response speed characteristics, and produce multi-color images.

The OLED may include a first electrode disposed on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially disposed on the first electrode. Holes supplied from the first electrode move to the emission layer through the hole transport region, and electrons supplied from the second electrode move to the emission layer through the electron transport region. Carriers such as holes and electrons recombine in the emission layer to generate excitons. These excitons change from an excited state to a ground state, thereby generating light.

Disclosure of Invention

One or more example embodiments include a blue fluorescent dopant compound having improved characteristics of high efficiency, low driving voltage, high luminance, and long lifetime, and an organic light emitting device including the same.

Additional aspects of the embodiments will be set forth in part in the description which follows, and in part will be obvious from the description, or may be learned by practice of the embodiments presented.

According to one or more exemplary embodiments, there is provided a compound represented by formula 1:

in the formula 1, the first and second groups,

R₁to R₄Can be independently selected from hydrogen, deuterium, -F, -Cl, -Br-I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, substituted or unsubstituted C₁-C₆₀Alkyl, substituted or unsubstituted C₂-C₆₀Alkenyl, substituted or unsubstituted C₂-C₆₀Alkynyl, substituted or unsubstituted C₁-C₆₀Alkoxy, substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₁-C₆₀A heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;

Ar₁to Ar₄May each be independently selected from substituted or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₁-C₆₀A heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;

x may be selected from oxygen (O), sulfur (S) and selenium (Se);

substituted C₁-C₆₀Alkyl, substituted C₂-C₆₀Alkenyl, substituted C₂-C₆₀Alkynyl, substituted C₁-C₆₀Alkoxy, substituted C₃-C₁₀Cycloalkyl, substituted C₂-C₁₀Heterocycloalkyl, substituted C₃-C₁₀Cycloalkenyl, substituted C₂-C₁₀Heterocycloalkenyl, substituted C₆-C₆₀Aryl, substituted C₆-C₆₀Aryloxy, substituted C₆-C₆₀Arylthio, substituted C₂-C₆₀At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:

deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl and C₁-C₆₀An alkoxy group;

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₂-C₆₀Heteroaryl, monovalent nonaromatic condensed polycyclic radical, monovalent nonaromatic condensed heteropolycyclic radical, -N (Q)₁₁)(Q₁₂)、-Si(Q₁₃)(Q₁₄)(Q₁₅) and-B (Q)₁₆)(Q₁₇) C of at least one of₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl and C₁-C₆₀An alkoxy group;

C₃-C₁₀cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₂-C₆₀Heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic condensed heteropolycyclic groups;

are each substituted by a group selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitroAmino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₂-C₆₀Heteroaryl, monovalent nonaromatic condensed polycyclic radical, monovalent nonaromatic condensed heteropolycyclic radical, -N (Q)₂₁)(Q₂₂)、-Si(Q₂₃)(Q₂₄)(Q₂₅) and-B (Q)₂₆)(Q₂₇) C of at least one of₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₂-C₆₀Heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic condensed heteropolycyclic groups; and

-Si(Q₃₁)(Q₃₂)(Q₃₃)，

wherein Q is₁₁To Q₁₇、Q₂₁To Q₂₇And Q₃₁To Q₃₃Can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₁-C₆₀Heteroaryl, monoMonovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic condensed heteropolycyclic groups.

According to one or more example embodiments, there is provided an organic light emitting device including: a first electrode; a second electrode facing the first electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes the compound represented by formula 1.

According to one or more example embodiments, there is provided a flat panel display apparatus including the organic light emitting device, a first electrode of the organic light emitting device being electrically coupled to a source electrode and a drain electrode of a thin film transistor.

Drawings

These and/or other aspects will become apparent and more readily appreciated from the following description of the exemplary embodiments, taken in conjunction with the accompanying drawings of which:

fig. 1 is a schematic cross-sectional view of an organic light emitting device according to an embodiment.

Detailed Description

Reference will now be made in greater detail to example embodiments, examples of which are illustrated in the accompanying drawings. In this regard, the present example embodiments may have different forms and should not be construed as limited to the descriptions set forth herein. Accordingly, only the exemplary embodiments are described below to explain aspects of the described embodiments by referring to the figures. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items. When a statement such as "at least one of" follows a column of elements, that modifies the entire column of elements rather than modifying individual elements of the column. In addition, the use of "may" in describing embodiments of the invention refers to "one or more embodiments of the invention.

Spatially relative terms such as "below … …," "below … …," "below," "above … …," "above," and the like may be used herein to describe one element or feature's relationship to another element or feature as illustrated in the figures for ease of explanation. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientation depicted in the figures. For example, if the device in the figures is turned over, elements described as "below" or "beneath" other elements or features would then be oriented "above" the other elements or features. Thus, the example terms "below … …" and "below … …" can encompass both an orientation of "above … …" and "below … …". For example, in the context of the present disclosure, the emissive layer may be above or below the first electrode. Additionally, the device may be otherwise positioned (e.g., rotated 90 degrees or at other orientations) and the spatially relative descriptors used herein interpreted accordingly.

Provided are compounds represented by formula 1:

formula 1

In the formula 1, the first and second groups,

R₁to R₄Can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, and substituted or unsubstituted C₁-C₆₀Alkyl, substituted or unsubstituted C₂-C₆₀Alkenyl, substituted or unsubstituted C₂-C₆₀Alkynyl, substituted or unsubstituted C₁-C₆₀Alkoxy, substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted orUnsubstituted C₂-C₁₀Heterocycloalkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₁-C₆₀A heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;

x may be selected from oxygen (O), sulfur (S) and selenium (Se);

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl, heteroaryl, and heteroaryl,C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₂-C₆₀Heteroaryl, monovalent nonaromatic condensed polycyclic radical, monovalent nonaromatic condensed heteropolycyclic radical, -N (Q)₂₁)(Q₂₂)、-Si(Q₂₃)(Q₂₄)(Q₂₅) and-B (Q)₂₆)(Q₂₇) C of at least one of₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₂-C₆₀Heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic condensed heteropolycyclic groups; and

-Si(Q₃₁)(Q₃₂)(Q₃₃)，

wherein Q is₁₁To Q₁₇、Q₂₁To Q₂₇And Q₃₁To Q₃₃Can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₁-C₆₀Heteroaryl, monovalent nonaromatic condensed polycyclic and monovalent nonaromatic condensed heteropolycyclic groups.

With respect to the related art blue light emitting material, a blue light emitting compound having a core structure of diphenylanthracene and including an aryl group substituted at an end (e.g., at a terminal) and an organic light emitting device including the blue light emitting compound have been used. However, such organic light emitting devices fail to exhibit sufficient or appropriate light emitting efficiency and luminance.

Compounds including substituted pyrene moieties and organic light emitting devices including pyrene compounds have been used in the art. However, such an organic light emitting device has difficulty in realizing deep blue due to low color purity of blue, and thus has a problem in realizing full color display of multiple colors.

In order to solve the above problems, embodiments of the present disclosure include a novel compound and an organic light emitting device including the novel compound.

The novel compounds of the present disclosure have excellent electrical characteristics, high electron transport ability and light emitting ability. In some embodiments, the novel compounds may have high glass transition temperatures and prevent crystallization (e.g., the crystallization temperature of the compounds may be increased), and thus, may be applicable to fluorescent and phosphorescent devices of all colors including red, green, blue, and white. The novel compounds can also be used to fabricate organic light emitting devices having high efficiency, low voltage, high brightness, and long lifetime characteristics.

The substituent of formula 1 will be described in more detail.

According to an exemplary embodiment, in formula 1, R₁To R₄May each independently be substituted or unsubstituted C₁-C₆₀An alkyl group.

According to an exemplary embodiment, in formula 1, Ar₁To Ar₄May each be independently selected from the group represented by formula 2a to formula 2 d:

in the formulae 2a to 2d,

H₁may be selected from CR₁₁R₁₂O and S;

R₁₁、R₁₂and Z₁Can all independently be selected fromIn the presence of hydrogen, deuterium, a halogen group, cyano, nitro, hydroxy, carboxyl, substituted or unsubstituted C₁-C₂₀Alkyl, substituted or unsubstituted C₆-C₂₀Aryl, substituted or unsubstituted C₁-C₂₀Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group and-Si (Q)₃₁)(Q₃₂)(Q₃₃) Wherein Q is₃₁To Q₃₃May be the same as described with respect to formula 1;

at a plurality of Z₁In the case of each Z₁May be the same as each other or different from each other (e.g., each Z₁With other Z₁The same or different);

p may be an integer selected from 1 to 9;

may refer to a binding site.

According to an example embodiment, in formula 1, X may be O or S.

According to an exemplary embodiment, the compound represented by formula 1 may be represented by one of formulae 2 to 4:

formula 2

Formula 3

Formula 4

The substituents of formulae 2 to 4 may be defined as described above. According to an exemplary embodiment, the compound represented by formula 1 may be one of the following compounds 1 to 128:

the term "organic layer" as used herein refers to a single layer and/or a plurality of layers disposed between a first electrode and a second electrode of an organic light emitting device. However, the material included in the "organic layer" is not limited to an organic compound. For example, the "organic layer" may include an inorganic compound.

Fig. 1 shows a schematic cross-sectional view of an organic light emitting device 10 according to an example embodiment. The organic light emitting device 10 has a structure of a first electrode 110, an organic layer 150, and a second electrode 190.

Hereinafter, a structure of an organic light emitting device according to example embodiments and a method of manufacturing an organic light emitting device according to example embodiments will be described with reference to the accompanying drawings.

In the embodiment shown in the figures, the substrate may additionally be disposed below the first electrode 110 and/or above the second electrode 190. The substrate may be a glass substrate or a transparent plastic substrate, each of which has excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, a material for forming the first electrode 110 may be selected from materials having a high work function to facilitate hole injection. The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 110 may be Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin oxide (SnO), each having transparency and excellent conductivity₂) Or zinc oxide (ZnO). In some embodiments, when the first electrode 110 is a semi-transparent electrode or a reflective electrode, at least one selected from magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) may be used as a material for forming the first electrode 110.

The first electrode 110 may be a single layer structure or a multi-layer structure including a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO, but the structure of the first electrode 110 is not limited thereto.

The organic layer 150 may be disposed on top of the first electrode 110 and may include an emission layer.

The organic layer 150 may further include a hole transport region disposed between the first electrode 110 and the emission layer and an electron transport region disposed between the emission layer and the second electrode 190.

The hole transport region may include at least one selected from a Hole Transport Layer (HTL), a Hole Injection Layer (HIL), a buffer layer, and an electron blocking layer, and the electron transport region may include at least one selected from a hole blocking layer HBL, an electron transport layer ETL, and an electron injection layer EIL, but the hole transport region and the electron transport region are not limited thereto.

The hole transport region may have a single-layer structure including a single material, a single-layer structure including a plurality of different materials, or a multi-layer structure including a plurality of layers formed of a plurality of different materials.

For example, the hole transport region may have a single layer structure or a structure of HIL/HTL, a structure of HIL/HTL/buffer layer, a structure of HIL/buffer layer, a structure of HTL/buffer layer, or a structure of HIL/HTL/EBL including a plurality of different materials. In the above structure, the layers of each structure are sequentially stacked in the stated order from the first electrode 110, but the hole transport region is not limited thereto.

When the hole transport region includes the HIL, the HIL may be formed on the first electrode 110 by using one or more suitable methods, such as vacuum deposition, spin coating, casting, a langmuir-bloggett (LB) method, inkjet printing, laser printing, or a Laser Induced Thermal Imaging (LITI) method.

When the HIL is formed by vacuum deposition, the vacuum deposition may be, for example, at a deposition temperature of about 100 ℃ to about 500 ℃, at about 10 ℃ in consideration of a compound for forming the HIL to be deposited and a structure of the HIL to be formed (for example, in consideration of characteristics of the deposited compound and characteristics of the formed HIL)^-8Is supported to about 10^-3Vacuum of tray and at aboutPer second to aboutDeposition rate per second was performed.

When the HIL is formed by spin coating, the coating may be performed, for example, at a coating speed of about 2,000rpm to about 5,000rpm and at a temperature of about 80 ℃ to about 200 ℃, in consideration of a compound for forming the HIL to be deposited and a structure of the HIL to be formed (for example, in view of characteristics of the coated compound and characteristics of the formed HIL).

When the hole transport region includes an HTL, the HTL may be formed on the first electrode 110 or the HIL by using one or more suitable methods, such as vacuum deposition, spin coating, casting, an LB method, inkjet printing, laser printing, or an LITI method. When the HTL is formed by vacuum deposition and/or spin coating, deposition and coating conditions for the HTL may be determined by referring to deposition and coating conditions for the HIL.

The hole transport region may include at least one selected from the group consisting of m-MTDATA, TDATA, 2-TNATA, NPB, β -NPB, TPD, spiro-NPB, α -NPB, TAPC, HMTPD, 4',4 ″ -tris (N-carbazolyl) triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly (4-styrenesulfonate) (PANI/PSS), a compound represented by formula 201, and a compound represented by formula 202:

formula 201

Formula 202

In the equations 201 and 202,

xa1 through xa4 may each be independently selected from 0, 1, 2, and 3,

xa5 may be selected from 1, 2,3, 4 and 5,

R₂₀₁to R₂₀₄May each be independently selected from substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₁-C₆₀Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic.

For example, in equations 201 and 202,

L₂₀₁to L₂₀₅May each be independently selected from:

phenylene, naphthylene, fluorenylene, spirofluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthracylene, pyrenyleneA group selected from the group consisting of pyridyl, pyrazinylene, pyrimidinyl, pyridazinylene, quinolinylene, isoquinolinylene, quinoxalinylene, quinazolinylene, carbazolyl and triazinylene; and

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, fluorenyl,pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinylAt least one of phenylene, naphthylene, fluorenylene, spirofluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthracenylene, pyrenylene, and pyrenyleneA group, a pyridylene group, a pyrazinylene group, a pyrimidylene group, a pyridazinylene group, a quinolylene group, an isoquinolylene group, a quinoxalylene group, a quinazolinylene group, a carbazolyl group and a triazinylene group,

xa1 through xa4 can each independently be 0, 1 or 2,

xa5 can be 1, 2 or 3,

R₂₀₁to R₂₀₄May each be independently selected from:

phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl,Phenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, and triazinyl; and

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, phenyl, naphthyl, azulenyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracyl, pyrenyl, azulenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracyl, pyrenyl, azulenyl, phenanthrenyl,Phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, and at least one of pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, and triazinyl,Pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl, and triazinyl.

The compound represented by formula 201 may be represented by formula 201A:

formula 201A

For example, the compound represented by formula 201 may be represented by formula 201A-1, but the compound is not limited thereto:

formula 201A-1

The compound represented by formula 202 may be represented by formula 202A, but the compound is not limited thereto:

formula 202A

In the formulae 201A, 201A-1 and 202A, L₂₀₁To L₂₀₃Xa1 to xa3, xa5 and R₂₀₂To R₂₀₄R can be understood by referring to the description provided in the specification₂₁₁And R₂₁₂Can be bound by reference to R₂₀₃The description is provided to understand that R₂₁₃To R₂₁₆Can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀Heteroaryl, monovalent nonaromatic condensed polycyclic and monovalent nonaromatic condensed heteropolycyclic groups.

For example, in formula 201A, formula 201A-1 and formula 202A,

L₂₀₁to L₂₀₃May each be independently selected from:

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, fluorenyl,phenylene, naphthylene, fluorenylene, spirofluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrenylene, anthracenylene, pyrenylene, and the like of at least one of a phenyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl groupA group, a pyridylene group, a pyrazinylene group, a pyrimidylene group, a pyridazinylene group, a quinolylene group, an isoquinolylene group, a quinoxalylene group, a quinazolinylene group, a carbazolyl group and a triazinylene group,

xa1 through xa3 may each independently be 0 or 1,

R₂₀₃、R₂₁₁and R₂₁₂May each be independently selected from:

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, fluorenyl,phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, and at least one of pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, and triazinyl,Phenyl, phenanthryl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl,

R₂₁₃and R₂₁₄May each be independently selected from:

C₁-C₂₀alkyl and C₁-C₂₀An alkoxy group;

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, and pyrenyl,C of at least one of phenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalyl, quinazolinyl, carbazolyl, and triazinyl₁-C₂₀Alkyl and C₁-C₂₀An alkoxy group;

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, fluorenyl,phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, and at least one of pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, and triazinyl,Pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl,

R₂₁₅and R₂₁₆May each be independently selected from:

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₂₀Alkyl and C₁-C₂₀An alkoxy group;

phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl,Phenyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, and triazinyl; and

xa5 can be 1 or 2.

In the formulae 201A and 201A-1, R₂₁₃And R₂₁₄Can be combined with each other (e.g., combined together) to form a saturated or unsaturated ring.

The compound represented by formula 201 and the compound represented by formula 202 may each include at least one selected from the following compounds HT1 through HT20, but the compounds are not limited thereto.

The thickness of the hole transport region may be aboutTo aboutWithin a range of, for example, aboutTo aboutWithin the range of (1). When the hole transport region includes the HIL and the HTL, the thickness of the HIL may be aboutTo less than aboutWithin a range of, for example, aboutTo aboutMay be in the range of aboutTo aboutWithin a range of, for example, aboutTo aboutWithin the range of (1). When the thicknesses of the hole transport region, the HIL, and the HTL are within these ranges, satisfactory or suitable hole transport characteristics are obtained without significantly increasing the driving voltage.

In addition to the above materials, the hole transport region may further include a charge generation material for improving the conductive property. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region.

The charge generating material may be, for example, a p-dopant. The p-dopant may be (for example, may be selected from) one of quinone derivatives, metal oxides, and cyano group-containing compounds, but the p-dopant is not limited thereto. For example, non-limiting examples of p-dopants include: quinone derivatives such as Tetracyanoquinodimethane (TCNQ) and 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinodimethane (F4-TCNQ); metal oxides such as tungsten oxide and molybdenum oxide; and the following compound HT-D1, but the p-dopant is not limited thereto.

The hole transport region may include an EBL and a buffer layer in addition to the HIL and the HTL. The buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, thereby improving light emitting efficiency of the formed organic light emitting device. As the material included in the buffer layer, a material included in the hole transporting region may be used. The EBL can reduce or prevent the injection of electrons from the electron transport region.

The emission layer may be formed on the first electrode 110 or on the hole transport region by using one or more suitable methods, such as vacuum deposition, spin coating, casting, an LB method, inkjet printing, laser printing, or LITI method. When the emission layer is formed by vacuum deposition and/or spin coating, deposition and coating conditions for the emission layer may be determined by referring to deposition and coating conditions for the HIL.

When the organic light emitting device 10 is a full-color organic light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, or a blue emission layer according to individual sub-pixels, respectively. The emission layer may have various suitable structural modifications, for example, may have a stacked structure of a red emission layer, a green emission layer, and a blue emission layer or a mixed structure of a red light emitting material, a green light emitting material, and a blue light emitting material mixed without distinction between layers, and thus, the emission layer may emit white light.

The emission layer may include a host and a dopant.

The host may comprise, for example, one selected from TPBi, TBADN, AND (also referred to as "DNA"), CBP, CDBP, AND TCP:

in some embodiments, the subject may include a compound represented by formula 301:

formula 301

Ar₃₀₁-[(L₃₀₁)_xb1-R₃₀₁]_xb2

In the formula 301, the process is carried out,

Ar₃₀₁may be selected from:

naphthyl, heptenylene, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenalkenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo [9,10 ] benzo]Phenanthryl, pyrenyl,Phenyl, tetracenyl, picenyl, peryleneyl, pentylphenyl, and indenonanthracenyl; and

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀Heteroaryl group, monovalent nonaromatic condensed polycyclic group, monovalent nonaromatic condensed heteropolycyclic group and-Si (Q)₃₀₁)(Q₃₀₂)(Q₃₀₃) (wherein, Q)₃₀₁To Q₃₀₃Can be independently selected from hydrogen and C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₆-C₆₀Aryl and C₁-C₆₀Heteroaryl) at least one of naphthyl, heptalenyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo [9,10 ] benzo]Phenanthryl, pyrenyl,Phenyl, tetracenyl, picenyl, perylenyl, pentylphenyl and indenonanthracenyl,

L₃₀₁can be combined with L by reference₂₀₁The description is provided for purposes of understanding and,

R₃₀₁may be selected from:

C₁-C₂₀alkyl and C₁-C₂₀An alkoxy group;

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, and pyrenyl,Pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, pyridazinyl, quinolinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinolyl,c of at least one of quinazolinyl, carbazolyl, and triazinyl₁-C₂₀Alkyl and C₁-C₂₀An alkoxy group,

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, fluorenyl,phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, and at least one of pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, and triazinyl,Pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl,

xb1 can be selected from 0, 1, 2 and 3,

xb2 may be selected from 1, 2,3 and 4.

For example, in the formula 301,

L₃₀₁may be selected from:

phenylene, naphthyleneFluorenyl, spirolenylidene, benzofluorenyl, dibenzofluorenyl, phenanthrylidene, anthracenylidene, pyrenylidene and pyrenylideneA group; and

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, andphenylene, naphthylene, fluorenylene, spirofluorenylene, benzofluorenylene, dibenzofluorenylene, phenanthrylene, anthracenylene, pyrenylene and pyrenylene of at least one of the radicalsThe base group is a group of a compound,

R₃₀₁may be selected from:

C₁-C₂₀alkyl and C₁-C₂₀An alkoxy group;

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl and pyrenylC of at least one of the radicals₁-C₂₀Alkyl and C₁-C₂₀An alkoxy group;

phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl anda group; and

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracenyl, pyrenyl, andphenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, anthracyl, pyrenyl, andbut the compound represented by formula 301 is not limited thereto.

For example, the subject may include a compound represented by formula 301A:

formula 301A

The substituents of formula 301A can be understood by reference to the description provided in this specification.

The compound represented by formula 301 may include at least one selected from the following compounds H1 to H42, but the compound represented by formula 301 is not limited thereto:

in some embodiments, the body may include at least one selected from the group consisting of compound H43 to compound H49 below, but the body is not limited thereto:

according to example embodiments, the dopant may include a compound represented by formula 1.

The amount of the dopant included in the emission layer may generally be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but the dopant is not limited thereto.

The thickness of the emissive layer may be aboutTo aboutWithin a range of, for example, aboutTo aboutWithin the range of (1). When the thickness of the emission layer is within the above-described range, excellent light emission characteristics are obtained without significantly increasing the driving voltage.

Next, an electron transport region may be disposed on the emission layer.

The electron transport region may include at least one selected from the group consisting of HBL, ETL, and EIL, but the electron transport region is not limited thereto.

When the electron transport region includes an HBL, the HBL may be formed on the emission layer by using one or more suitable methods, such as vacuum deposition, spin coating, casting, an LB method, inkjet printing, laser printing, or an LITI method. When the HBL is formed by vacuum deposition and/or spin coating, deposition and coating conditions for the HBL may be determined by referring to deposition and coating conditions for the HIL.

The HBL may include, for example, at least one selected from the following BCP and Bphen, but the HBL is not limited thereto:

the thickness of the HBL may be aboutTo aboutWithin a range of, for example, aboutTo aboutWithin the range of (1). When the thickness of the HBL is within the range described above, excellent hole blocking characteristics are obtained without significantly increasing the driving voltage.

The electron transport region may have the structure ETL/EIL or the structure HBL/ETL/EIL. In the above structure, the layers of each structure are sequentially stacked from the emission layer, but the electron transport region is not limited thereto.

According to example embodiments, the organic layer 150 of the organic light emitting device 10 may include an electron transport region between the emission layer and the second electrode 190, and the electron transport region may include an ETL. The ETL may include a plurality of layers. For example, the electron transport region may include a first electron transport layer and a second electron transport layer.

The ETL may comprise a BCP, Bphen, Alq selected from₃At least one of Balq, TAZ and NTAZ:

in some embodiments, the ETL may include at least one selected from the group consisting of a compound represented by formula 601 and a compound represented by formula 602:

formula 601

Ar₆₀₁-[(L₆₀₁)_xe1-E₆₀₁]_xe2

In the formula 601, the first and second groups,

Ar₆₀₁may be selected from:

naphthyl, heptenylene, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenalkenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo [9,10 ] benzo]Phenanthryl, pyrenyl,Phenyl, tetracenyl, picenyl, peryleneyl, pentylphenyl, and indenonanthracenyl;

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₃-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₃-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₂-C₆₀Heteroaryl group, monovalent nonaromatic condensed polycyclic group, monovalent nonaromatic condensed heteropolycyclic group and-Si (Q)₃₀₁)(Q₃₀₂)(Q₃₀₃) (wherein, Q)₃₀₁To Q₃₀₃Can be independently selected from hydrogen and C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₆-C₆₀Aryl and C₂-C₆₀Heteroaryl) at least one of naphthyl, heptalenyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo [9,10 ] benzo]Phenanthryl, pyrenyl,Phenyl, tetracenyl, picenyl, perylenyl, pentylphenyl and indenonanthracenyl,

L₆₀₁l may be incorporated herein by reference₂₀₃The description is provided for purposes of understanding and,

E₆₀₁may be selected from:

pyrrolyl, thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl and imidazopyrimidinyl; and

are each substituted by a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyCyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenaphthenyl, acenaphthenyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo [9,10 ] benzo]Phenanthryl, pyrenyl,A pyrrolyl group, at least one of a pyrrolyl group, a tetracenyl group, a picenyl group, a peryleneyl group, a pentylenyl group, a hexacenyl group, a pentacenyl group, a rubicinyl group, a coronenyl group, an egg phenyl group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothienyl group, an isothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl, Thienyl, furyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzooxazolyl, isothiazolyl, tetrazolyl, pyrazinyl, phenanthridinyl, benzofuranyl, benzothienyl, isothiazolyl, quinoxalinyl, quinoxalCarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl and imidazopyrimidinyl,

xe1 may be selected from 0, 1, 2 and 3,

xe2 may be selected from 1, 2,3, and 4.

Formula 602

In the equation 602, in the case of the equation,

X₆₁₁can be N or C- (L)₆₁₁)_xe611-R₆₁₁，X₆₁₂Can be N or C- (L)₆₁₂)_xe612-R₆₁₂，X₆₁₃Can be N or C- (L)₆₁₃)_xe613-R₆₁₃Wherein X is₆₁₁To X₆₁₃Is nitrogen (N).

L₆₁₁To L₆₁₆L may be incorporated herein by reference₂₀₃The description is provided for purposes of understanding and,

R₆₁₁to R₆₁₆May each be independently selected from:

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₂₀Alkyl radical, C₁-C₂₀Alkoxy, phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, fluorenyl, or the like,Dibenzofluorenyl group, phenanthryl group, anthracenyl group, pyrenyl group,Phenyl, naphthyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, anthracenyl, pyrenyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, triazinyl, and at least one of pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, carbazolyl, and triazinyl,Pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolinyl, isoquinolinyl, quinoxalinyl, quinazolinyl, carbazolyl and triazinyl,

xe611 through xe616 may each be independently selected from 0, 1, 2, and 3.

The compound represented by formula 601 and the compound represented by formula 602 may each include at least one selected from the following compounds ET1 to ET 15:

the thickness of the ETL may be aboutTo aboutWithin a range of, for example, aboutTo aboutWithin the range of (1). When the thickness of the ETL is within the above-described range, the ETL has satisfactory or suitable electron transport characteristics without significantly increasing the driving voltage.

In addition to the materials described above, the ETL can also include a metal-containing material.

The metal-containing material may include a Li complex. Li complexes may include, for example, the compound ET-D1 (lithium quinolinolate, LiQ)) or the following compound ET-D2:

the electron transport region may include an EIL that facilitates injection of electrons from the second electrode 190.

The EIL may be formed on the ETL by using one or more suitable methods, such as vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing, or LITI method. When the EIL is formed by vacuum deposition and/or spin coating, deposition and coating conditions for the EIL may be determined by referring to deposition and coating conditions for the HIL.

The EIL may comprise one or more selected from LiF, NaCl, CsF, Li₂O, BaO and LiQ.

The thickness of the EIL may be aboutTo aboutWithin a range of, for example, aboutTo aboutWithin the range of (1). When the thickness of the EIL is within the range described above, the EIL has satisfactory or suitable electron injection characteristics without significantly increasing the driving voltage.

The second electrode 190 is disposed on the organic layer 150. The second electrode 190 may be a cathode as an electron injection electrode. Here, the material for forming the second electrode 190 may include a metal, an alloy, a conductive compound, or a mixture thereof having a relatively low work function. Examples of the material for forming the second electrode 190 include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), and magnesium-indium (Mg-In), magnesium-silver (Mg-Ag). In some embodiments, the material used to form the second electrode 190 may be ITO or IZO. The second electrode 190 may be a reflective electrode, a semi-transparent electrode, or a transparent electrode.

The organic layer 150 of the organic light emitting device 10 may be formed by a deposition method using the compound according to example embodiments or by a wet coating method using the compound prepared in solution according to example embodiments.

The organic light emitting device 10 according to example embodiments may be included in various suitable types of flat panel display devices, such as passive matrix OLED display devices and active matrix OLED display devices. For example, when the organic light emitting device 10 is equipped with an active matrix OLED display device, the first electrode 110 disposed on one side of the substrate may serve as a pixel electrode and may be electrically coupled to source and drain electrodes of a thin film transistor. In some embodiments, the organic light emitting device 10 may be equipped with a flat panel display apparatus that may have display screens on both sides.

In the above, the organic light emitting device 10 has been described with reference to the drawings, but the organic light emitting device is not limited thereto.

Hereinafter, representative substituents among all substituents used in the present disclosure may be defined as follows (the carbon number of the defined substituents is non-limiting and does not limit the characteristics of the substituents, and if substituents not described in the present disclosure are found in the general definition of the substituents, these substituents are not included, for example, the substituents not described herein should have the same meaning as commonly understood by one of ordinary skill in the art to which the present disclosure belongs).

As used herein, the term "C₁-C₆₀The alkyl group "means a straight or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl groups. As used herein, except C₁-C₆₀Alkylene is divalent rather than monovalent, the term "C₁-C₆₀Alkylene "means with C₁-C₆₀The alkyl groups have substantially the same structure.

As used herein, the term "C₁-C₆₀Alkoxy "means a group consisting of-OA₁₀₁(wherein, A)₁₀₁And C₁-C₆₀Alkyl groups are the same), and examples thereof include methoxy group, ethoxy group, and isopropoxy group.

As used herein, the term "C₂-C₆₀Alkenyl "means through C₂-C₆₀Examples of the hydrocarbon group formed by substituting at least one carbon-carbon double bond in the main chain of the alkyl group (for example, in the middle of the chain) or at the terminal include an ethenyl group, a propenyl group and a butenyl group. As used herein, except C₂-C₆₀Alkenylene is divalent rather than monovalent, the term "C₂-C₆₀Alkenylene refers to the group with C₂-C₆₀The alkenyl groups are divalent groups having substantially the same structure.

As used herein, the term "C₂-C₆₀Alkynyl "means through C₂-C₆₀Examples of the hydrocarbon group formed by substituting at least one carbon-carbon triple bond in the main chain of the alkyl group (for example, in the middle of the chain) or at the terminal include an ethynyl group and a propynyl group. As used herein, except C₂-C₆₀Alkynylene is other than divalent rather than monovalent, the term "C₂-C₆₀Alkynylene "means with C₂-C₆₀Alkynyl groups are divalent radicals having essentially the same structure.

As used herein, the term "a" or "an" refers to,the term "C₃-C₁₀Cycloalkyl "refers to a monovalent monocyclic hydrocarbon group having 3 to 10 carbon atoms, and examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. As used herein, except C₃-C₁₀Cycloalkylene being other than divalent rather than monovalent, the term "C₃-C₁₀Cycloalkylene "means a compound with C₃-C₁₀Cycloalkyl groups are divalent radicals having substantially the same structure.

As used herein, the term "C₁-C₁₀The heterocycloalkyl group "means a monovalent monocyclic group having at least one hetero atom of N, O, P and S as a ring-forming atom and carbon atoms of 1 to 10, and examples thereof include a tetrahydrofuranyl group and a tetrahydrothienyl group. As used herein, except C₂-C₁₀Heterocycloalkylene is divalent rather than monovalent, the term "C₂-C₁₀Heterocycloalkylene "means a group with C₂-C₁₀Heterocycloalkyl groups are divalent radicals having substantially the same structure.

As used herein, the term "C₃-C₁₀Cycloalkenyl "means having 3 to 10 carbon atoms and at least one double bond (e.g., at least one carbon-carbon double bond) in its ring without aromaticity (e.g., ring or C)₃-C₁₀Cycloalkenyl is not aromatic), examples of which include cyclopentenyl, cyclohexenyl, and cycloheptenyl. As used herein, except C₃-C₁₀Cycloalkenylene is divalent rather than monovalent, the term "C₃-C₁₀Cycloalkenyl is taken to mean radicals with C₃-C₁₀Cycloalkenyl groups are divalent radicals having essentially the same structure.

As used herein, the term "C₂-C₁₀Heterocycloalkenyl "refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, P and S as a ring-forming atom, 2 to 10 carbon atoms, and at least one double bond (e.g., at least one carbon-carbon double bond) in its ring. C₂-C₁₀Examples of heterocycloalkenyl include 2, 3-hydrofuranyl and 2, 3-hydrothienyl. As used herein, except C₂-C₁₀Heterocycloalkenylene is divalent rather than monovalent, the term "C₂-C₁₀Heterocycloalkenylene "means a group with C₂-C₁₀Heterocycloalkenyl groups are divalent radicals having substantially the same structure.

As used herein, the term "C₆-C₆₀Aryl "refers to a monovalent group having a carbocyclic aromatic system comprising 6 to 60 carbon atoms, as used herein, the term" C₆-C₆₀Arylene "refers to a divalent group having a carbocyclic aromatic system comprising 6 to 60 carbon atoms. C₆-C₆₀Examples of the aryl group include phenyl, naphthyl, anthryl, phenanthryl, pyrenyl andand (4) a base. When C is present₆-C₆₀Aryl and C₆-C₆₀When the arylene groups each include two or more rings, the rings may be fused to each other (e.g., joined together).

As used herein, the term "C₁-C₆₀Heteroaryl "refers to a monovalent group having a carbocyclic aromatic system comprising at least one heteroatom selected from N, O, P and S as a ring-forming atom and 1 to 60 carbon atoms. As used herein, the term "C₁-C₆₀Heteroarylene "refers to a divalent group having a carbocyclic aromatic system comprising at least one heteroatom selected from N, O, P and S as a ring-forming atom and 1 to 60 carbon atoms. C₁-C₆₀Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl. When C is present₁-C₆₀Heteroaryl and C₁-C₆₀When the heteroarylenes each include two or more rings, the rings may be fused to each other (e.g., joined together).

As used herein, the term "C₆-C₆₀Aryloxy means-OA₁₀₂(wherein, A)₁₀₂Is C₆-C₆₀Aryl), as used herein, the term "C₆-C₆₀Arylthio "means-SA₁₀₃(wherein, A)₁₀₃Is C₆-C₆₀Aryl).

As used herein, the term "monovalent non-aromatic condensed polycyclic group" (e.g., a group having 8 to 60 carbon atoms) refers to a monovalent group having two or more rings fused to each other (e.g., bonded together), having only carbon atoms as ring-constituting atoms, and having non-aromaticity throughout the molecular structure (e.g., the entire monovalent non-aromatic condensed polycyclic group has no aromaticity although the group may be bonded to another group having aromaticity). An example of a monovalent non-aromatic condensed polycyclic group is a fluorenyl group. As used herein, the term "divalent non-aromatic condensed polycyclic group" refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensed polycyclic group, except that the divalent non-aromatic condensed polycyclic group is divalent rather than monovalent.

As used herein, the term "monovalent non-aromatic condensed heteromulticyclic group" (e.g., a group having 2 to 60 carbon atoms) refers to a monovalent group having two or more rings fused (e.g., bonded) to each other, having a heteroatom selected from N, O, P and S as a ring-forming atom in addition to C, and having non-aromaticity in the entire molecular structure (e.g., the entire monovalent non-aromatic condensed heteromulticyclic group has no aromaticity although the group may be bonded to another group having aromaticity). An example of a monovalent non-aromatic condensed heteropolycyclic group is a carbazolyl group. As used herein, the term "divalent non-aromatic condensed heteromulticyclic group" refers to a divalent group having substantially the same structure as a monovalent non-aromatic condensed heteromulticyclic group, except that the divalent non-aromatic condensed heteromulticyclic group is divalent rather than monovalent.

Substituted C₃-C₁₀Cycloalkylene, substituted C₂-C₁₀Heterocycloalkylene, substituted C₃-C₁₀Cycloalkenylene, substituted C₂-C₁₀Heterocycloalkenylene, substituted C₆-C₆₀Arylene, substituted C₁-C₆₀Heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C₁-C₆₀Alkyl, substituted C₂-C₆₀Alkenyl, substituted C₂-C₆₀Alkynyl, substituted C₁-C₆₀Alkoxy, substituted C₃-C₁₀Cycloalkyl, substituted C₂-C₁₀Heterocycloalkyl, substituted C₃-C₁₀Cycloalkenyl, substituted C₂-C₁₀Heterocycloalkenyl, substituted C₆-C₆₀Aryl, substituted C₆-C₆₀Aryloxy, substituted C₆-C₆₀Arylthio, substituted C₁-C₆₀At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀Heteroaryl, monovalent nonaromatic condensed polycyclic radical, monovalent nonaromatic condensed heteropolycyclic radical, -N (Q)₁₁)(Q₁₂)、-Si(Q₁₃)(Q₁₄)(Q₁₅) and-B (Q)₁₆)(Q₁₇) C of at least one of₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl and C₁-C₆₀An alkoxy group;

C₃-C₁₀cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀Heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic condensed heteropolycyclic groups;

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀Heteroaryl, monovalent nonaromatic condensed polycyclic radical, monovalent nonaromatic condensed heteropolycyclic radical, -N (Q)₂₁)(Q₂₂)、-Si(Q₂₃)(Q₂₄)(Q₂₅) and-B (Q)₂₆)(Q₂₇) C of at least one of₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₁-C₆₀Heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic condensed heteropolycyclic groups; and

-N(Q₃₁)(Q₃₂)、-Si(Q₃₃)(Q₃₄)(Q₃₅) and-B (Q)₃₆)(Q₃₇)，

Wherein Q is₁₁To Q₁₇、Q₂₁To Q₂₇And Q₃₁To Q₃₇Can all beIndependently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₁-C₆₀Heteroaryl, monovalent nonaromatic condensed polycyclic and monovalent nonaromatic condensed heteropolycyclic groups.

For example, substituted C₃-C₁₀Cycloalkylene, substituted C₂-C₁₀Heterocycloalkylene, substituted C₃-C₁₀Cycloalkenylene, substituted C₂-C₁₀Heterocycloalkenylene, substituted C₆-C₆₀Arylene, substituted C₁-C₆₀Heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C₁-C₆₀Alkyl, substituted C₂-C₆₀Alkenyl, substituted C₂-C₆₀Alkynyl, substituted C₁-C₆₀Alkoxy, substituted C₃-C₁₀Cycloalkyl, substituted C₂-C₁₀Heterocycloalkyl, substituted C₃-C₁₀Cycloalkenyl, substituted C₂-C₁₀Heterocycloalkenyl, substituted C₆-C₆₀Aryl, substituted C₆-C₆₀Aryloxy, substituted C₆-C₆₀Arylthio, substituted C₁-C₆₀At least one substituent of the heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenaphthyl, acenaphthenyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenaenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo [9,10 ] benzo]Phenanthryl, pyrenyl,A group selected from the group consisting of a phenyl group, a tetracenyl group, a picenyl group, a peryleneyl group, a pentylenyl group, a hexacenyl group, a pentacenyl group, a rubicene group, a coronenyl group, an egg phenyl group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothienyl group, an isothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a, Imidazopyrimidinyl, -N (Q)₁₁)(Q₁₂)、-Si(Q₁₃)(Q₁₄)(Q₁₅) and-B (Q)₁₆)(Q₁₇) C of at least one of₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl and C₁-C₆₀An alkoxy group;

cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentalenyl, indeneAryl, naphthyl, azulenyl, heptalenyl, indacenaphthenyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo [9,10 ] benzo]Phenanthryl, pyrenyl,A group, a tetracenyl group, a picenyl group, a perylene group, an amylene group, a hexacenyl group, a pentacenyl group, a rubicene group, a coronenyl group, an egg phenyl group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl, and imidazopyrimidinyl;

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenaphthenyl, acenaphthenyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo [9,10 ] benzo]Phenanthryl, pyrenyl,Phenyl, tetracenyl, picene, perylene, pentapheny, hexacene, pentacene, rubicene, coronenyl, etc,An egg-phenyl group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, an isoquinolyl group, a benzoquinolyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothienyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group₂₁)(Q₂₂)、-Si(Q₂₃)(Q₂₄)(Q₂₅) and-B (Q)₂₆)(Q₂₇) Cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenaphthenyl, acenaphthenyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo [9,10 ] benzo]Phenanthryl, pyrenyl,A group, a tetracenyl group, a picenyl group, a perylene group, an amylene group, a hexacenyl group, a pentacenyl group, a rubicene group, a coronenyl group, an egg phenyl group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazo.Pyridyl and imidazopyrimidinyl; and

Wherein Q is₁₁To Q₁₇、Q₂₁To Q₂₇And Q₃₁To Q₃₇Can be independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclopentenyl, cyclohexenyl, phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenaphthenyl, acenaphthenyl, fluorenyl, spirofluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo [9,10 ] benzo]Phenanthryl, pyrenyl,A group, a tetracenyl group, a picenyl group, a perylene group, an amylene group, a hexacenyl group, a pentacenyl group, a rubicene group, a coronenyl group, an egg phenyl group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolyl group, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzoxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl, and imidazopyrimidinyl.

As used herein, the term "Ph "refers to phenyl, as used herein, the term" Me "refers to methyl, as used herein, the term" Et "refers to ethyl, as used herein, the term" ter-Bu "or" Bu^t"means t-butyl.

Hereinafter, the organic light emitting device according to the embodiment will be described in more detail with reference to synthesis examples and examples.

Synthesis examples

Synthetic example 1: synthesis of intermediate A]

Synthesis of intermediate A-1

Under nitrogen atmosphere, 5.13g (30mmol) of thiophene-2, 5-diyl diboronic acid, 7.472g (30mmol) of methyl 2-bromo-5-chlorobenzoate, 1.732g (1.5mmol) of Pd (PPh)₃)₄And 6.21g (45mmol) of K₂CO₃THF/H dissolved in 500mL₂O (in a volume ratio of 2/1), and then stirred at a temperature of 80 ℃ for 12 hours. After the reaction solution was cooled to room temperature, 100mL of water was added thereto, and the resulting solution was extracted 3 times with 150mL of diethyl ether. The organic solvent collected therefrom was dried over magnesium sulfate, and then, the residue obtained by evaporating the solvent was isolated and purified by silica gel column chromatography, thereby obtaining 6.21g of intermediate A-1(21mmol, yield: 83%).

Synthesis of intermediate A-2

6.97g of intermediate A-2(15mmol, yield: 71%) was obtained in the same manner as in the synthesis of intermediate A-1 except that intermediate A-1 and methyl 5-bromo-2-iodobenzoate were used in place of thiophene-2, 5-diyl diboronic acid and methyl 2-bromo-5-chlorobenzoate, respectively.

Synthesis of intermediate A-3

6.97g (15mmol) of intermediate A-1 were dissolved in 500mL of anhydrous THF under a nitrogen atmosphere, followed by stirring at 0 ℃ for 1 hour. To this was slowly added dropwise 30mL of a 1.6M methylmagnesium bromide hexane solution for 1 hour, and then stirred at room temperature for 24 hours. Successively, 50mL of 1N HCl was added thereto, and the resulting solution was extracted 3 times with 150mL of diethyl ether. The organic solvent layer collected therefrom was dried over magnesium sulfate, and then, the residue obtained by evaporating the solvent was separated and purified by silica gel column chromatography, thereby obtaining 6.51g of intermediate A-3(14mmol, yield: 93%).

Synthesis of intermediate A

6.51g (14mmol) of intermediate A-3 was dissolved in 100mL of dichloromethane under a nitrogen atmosphere, and then stirred at a temperature of 0 ℃ for 1 hour. To this was slowly added dropwise 5mL of methanesulfonic acid for 30 minutes. After the reaction solution was stirred at room temperature for 1 hour, 50mL of an aqueous sodium carbonate solution was added thereto, and the resulting solution was extracted 3 times with 50mL of dichloromethane. The organic solvent layer collected therefrom was dried over magnesium sulfate, and then the residue obtained by evaporating the solvent was isolated and purified by silica gel column chromatography, thereby obtaining 4.29g of intermediate A (10mmol, yield: 71%).

Synthetic example 2: synthesis of intermediate B

Synthesis of intermediate B-1

6.16g of intermediate B-1(22mmol,

yield: 73%).

Synthesis of intermediate B-2

7.18g of intermediate B-2(16mmol, yield: 72%) was obtained in the same manner as for the synthesis of intermediate A-2 except that intermediate B-1 was used instead of intermediate A-1.

Synthesis of intermediate B-3

6.26g of intermediate B-3(13mmol, yield: 81%) was obtained in the same manner as described for the synthesis of intermediate A-3, except that intermediate B-2 was used instead of intermediate A-2.

Synthesis of intermediate B

4.54g of intermediate B (11mmol, yield: 84%) was obtained in the same manner as described for the synthesis of intermediate A except that intermediate B-3 was used instead of intermediate A-2.

[ Synthesis example 3: synthesis of Compound 1

Under nitrogen atmosphere, 0.429g (1mmol) of intermediate A, 0.507g (3mmol) of benzidine, 0.091g (0.1mmol) of tris (dibenzylideneacetone) dipalladium (0) (Pd)₂(dba)₃) 0.020g (0.1mmol) of tri-tert-butylphosphine (P (t-Bu)₃) And 0.288g (3mmol) of NaOtBu was dissolved in 60mL of toluene, followed by stirring at 90 ℃ for 4 hours. After the reaction solution was cooled to room temperature, the resulting solutions were each extracted 3 times with 50mL of water and 50mL of diethyl ether. The organic layer collected therefrom was dried over magnesium sulfate, and then, the residue obtained by evaporating the solvent was isolated and purified by silica gel column chromatography, thereby obtaining 0.520g of compound 1(0.8mmol, yield: 80%).

Synthetic example 4: synthesis of Compound 39

Synthesis of intermediate 39-1

0.500g of intermediate 39-1(0.87mmol, yield: 87%) was obtained in the same manner as described for the synthesis of compound 1 except that N-phenyl-4- (trimethylsilyl) aniline was used instead of benzidine.

Synthesis of Compound 39

0.540g of compound 39(0.7mmol, yield: 80%) was obtained in the same manner as described for the synthesis of compound 1 except that intermediate 39-1 and N-phenylnaphthalene-2-amine were used instead of intermediate A and benzidine, respectively.

Other additional compounds were synthesized according to the same synthetic route and the same synthetic method as described above, except that intermediate materials suitable for each synthesis were used in the additional synthesis. In addition to the compounds described in the present specification, one of ordinary skill in the art can readily synthesize other compounds in view of the present specification by referencing the synthetic routes and starting materials described above.

Example 1

As an anode substrate, 15. omega./cm was used² An ITO glass substrate (manufactured by Corning) was cut into a size of 50mm × 50mm × 0.7.7 mm, and ultrasonically cleaned with isopropyl alcohol and pure water for 5 minutes each, the ITO glass substrate was irradiated with ultraviolet light (UV) for 30 minutes, cleaned by exposure to ozone, and then transferred to a vacuum evaporator.

Vacuum depositing 2-TNATA on an ITO anode to form a ITO anodeOf 4,4' -bis [ N- (1-naphthyl) -N-phenylamino ] on the HIL]Biphenyl (NPB) to form a compound havingHTL of thickness of。

Then, the following 9, 10-dinaphthalen-2-yl-anthracenyl (DNA) and compound 1 were co-deposited on the HTL at a weight ratio of 98:2 to form a film having a structure ofThe thickness of the emission layer of (1).

Then, depositing Alq on the emitting layer₃To form a film havingAnd depositing LiF on the ETL to form an ETL having a thickness ofThe thickness of (a) is as follows. Depositing Al on the EIL to form a film havingThe second electrode (i.e., cathode) to thereby fabricate an organic light-emitting device.

Example 2

An organic light-emitting device was manufactured in the same manner as described with respect to example 1, except that compound 20 was used instead of compound 1 in forming the EML.

Example 3

An organic light-emitting device was manufactured in the same manner as described with respect to example 1, except that compound 39 was used instead of compound 1 in forming the EML.

Example 4

An organic light-emitting device was manufactured in the same manner as described with respect to example 1, except that compound 49 was used instead of compound 1 in forming the EML.

Example 5

An organic light-emitting device was manufactured in the same manner as described with respect to example 1, except that compound 70 was used instead of compound 1 in forming the EML.

Example 6

An organic light-emitting device was manufactured in the same manner as described with respect to example 1, except that compound 93 was used instead of compound 1 in forming the EML.

Example 7

An organic light-emitting device was manufactured in the same manner as described with respect to example 1, except that compound 98 was used instead of compound 1 in forming the EML.

Example 8

An organic light-emitting device was manufactured in the same manner as described with respect to example 1, except that the compound 125 was used instead of the compound 1 in forming the EML.

Comparative example 1

An organic light-emitting device was fabricated in the same manner as described with respect to example 1, except that DPAVBi, which has been used in the art as a blue fluorescent dopant, was used instead of compound 1 in forming the emission layer.

Characteristics of the organic light emitting devices manufactured in examples 1 to 8 and comparative example 1 are shown in table 1 below.

TABLE 1

Referring to table 1, it can be confirmed that, when the compound of formula 1 is used as a dopant for forming an emission layer, the driving voltage of the light emitting device including the compound represented by formula 1 is lower than that of the light emitting device of comparative example 1. The light emitting device including the compound represented by formula 1 also exhibits significantly improved efficiency and I-V-L characteristics, and in particular, shows excellent life characteristics.

As described above, the organic light emitting device including the compound according to one or more embodiments described above may have good emission characteristics, and thus may be suitable for fluorescent devices and/or phosphorescent devices of all colors including red, green, blue, and white. Therefore, an organic light emitting device having characteristics of high efficiency, low driving voltage, high luminance, and long lifetime can be manufactured.

It will be understood that when an element or layer is referred to as being "on," "connected to" or "coupled to" another element or layer, it can be directly on, connected or coupled to the other element or layer or one or more intervening elements or layers may be present. For example, in the context of the present disclosure, the emissive layer may be directly or indirectly on the hole transport region. In addition, it will also be understood that when an element or layer is referred to as being "between" two elements or layers, it can be the only element or layer between the two elements or layers, or one or more intervening elements or layers may also be present.

It is to be understood that the example embodiments described herein are to be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each example embodiment are generally considered applicable to other similar features or aspects in other example embodiments.

Although one or more exemplary embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present disclosure as defined by the following claims and their equivalents.

Claims

1. A compound represented by formula 1:

formula 1

Wherein,

R₁to R₄Are all independently selected from:

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group orSalts thereof, sulfonic acid groups or salts thereof, phosphoric acid groups or salts thereof, substituted or unsubstituted C₁-C₆₀Alkyl, substituted or unsubstituted C₂-C₆₀Alkenyl, substituted or unsubstituted C₂-C₆₀Alkynyl, substituted or unsubstituted C₁-C₆₀Alkoxy, substituted or unsubstituted C₃-C₁₀Cycloalkyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkyl, substituted or unsubstituted C₃-C₁₀Cycloalkenyl, substituted or unsubstituted C₂-C₁₀Heterocycloalkenyl, substituted or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₆-C₆₀Aryloxy, substituted or unsubstituted C₆-C₆₀Arylthio, substituted or unsubstituted C₁-C₆₀A heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

Ar₁to Ar₄Are all independently selected from substituted or unsubstituted C₆-C₆₀Aryl, substituted or unsubstituted C₁-C₆₀A heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;

x is selected from the group consisting of oxygen, sulfur and selenium,

substituted C₁-C₆₀Alkyl, substituted C₂-C₆₀Alkenyl, substituted C₂-C₆₀Alkynyl, substituted C₁-C₆₀Alkoxy, substituted C₃-C₁₀Cycloalkyl, substituted C₂-C₁₀Heterocycloalkyl, substituted C₃-C₁₀Cycloalkenyl, substituted C₂-C₁₀Heterocycloalkenyl, substituted C₆-C₆₀Aryl, substituted C₆-C₆₀Aryloxy, substituted C₆-C₆₀Arylthio, substituted C₂-C₆₀At least one substituent of the heteroaryl, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed heteropolycyclic group is selected from the group consisting of:

each substituted with a group selected from deuterium, -F, -Cl, -Br, -I, hydroxy, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀CycloalkanesBase, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₂-C₆₀Heteroaryl, monovalent nonaromatic condensed polycyclic radical, monovalent nonaromatic condensed heteropolycyclic radical, -N (Q)₂₁)(Q₂₂)、-Si(Q₂₃)(Q₂₄)(Q₂₅) and-B (Q)₂₆)(Q₂₇) C of at least one of₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₆-C₆₀Aryloxy radical, C₆-C₆₀Arylthio group, C₂-C₆₀Heteroaryl, monovalent non-aromatic condensed polycyclic and monovalent non-aromatic condensed heteropolycyclic groups; and

-Si(Q₃₁)(Q₃₂)(Q₃₃)，

wherein Q is₁₁To Q₁₇、Q₂₁To Q₂₇And Q₃₁To Q₃₃Are independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C₁-C₆₀Alkyl radical, C₂-C₆₀Alkenyl radical, C₂-C₆₀Alkynyl, C₁-C₆₀Alkoxy radical, C₃-C₁₀Cycloalkyl radical, C₂-C₁₀Heterocycloalkyl radical, C₃-C₁₀Cycloalkenyl radical, C₂-C₁₀Heterocycloalkenyl, C₆-C₆₀Aryl radical, C₁-C₆₀Heteroaryl, monovalent nonaromatic condensed polycyclic and monovalent nonaromatic condensed heteropolycyclic groups.

2. The compound according to claim 1, wherein, in formula 1, R₁To R₄Are each independently substituted or unsubstituted C₁-C₆₀An alkyl group.

3. The compound according to claim 1, wherein, in formula 1, Ar₁To Ar₄Are each independently selected from the group represented by formula 2a to formula 2 d:

wherein, in formulae 2a to 2d,

H₁is selected from the group consisting of CR₁₁R₁₂The total content of the components O and S,

R₁₁、R₁₂and Z₁Are independently selected from hydrogen, deuterium, halogen group, cyano, nitro, hydroxyl, carboxyl, substituted or unsubstituted C₁-C₂₀Alkyl, substituted or unsubstituted C₆-C₂₀Aryl, substituted or unsubstituted C₁-C₂₀Heteroaryl, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group and-Si (Q)₃₁)(Q₃₂)(Q₃₃)，

Wherein when the compound comprises a plurality of Z₁Each Z is₁With other Z₁The same or different, and the same or different,

p is an integer selected from 1 to 9,

indicates the binding site.

4. The compound according to claim 1, wherein, in formula 1, X is O or S.

5. The compound of claim 1, wherein the compound of formula 1 is represented by formula 2:

formula 2

6. The compound of claim 1, wherein the compound of formula 1 is represented by formula 3:

formula 3

7. The compound of claim 1, wherein the compound of formula 1 is represented by formula 4:

formula 4

8. The compound according to claim 1, wherein the compound represented by formula 1 is one of the following compounds:

9. an organic light emitting device, comprising:

a first electrode;

a second electrode facing the first electrode; and

an organic layer between the first electrode and the second electrode, wherein the organic layer comprises an emissive layer and the compound of claim 1.

10. The organic light emitting device of claim 9, wherein the organic layer is formed by a wet coating method.

11. The organic light emitting device according to claim 9, wherein the first electrode is an anode,

the second electrode is a cathode and the second electrode is a cathode,

the organic layer includes: i) a hole transport region between the first electrode and the emission layer and including at least one selected from a hole injection layer, a hole transport layer, and an electron blocking layer; and ii) an electron transport region between the emission layer and the second electrode and including at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

12. An organic light-emitting device according to claim 11 wherein the emissive layer comprises a compound according to claim 1.

13. An organic light-emitting device according to claim 11 wherein the emissive layer comprises a compound according to claim 1 as a dopant.

14. An organic light-emitting device according to claim 11 wherein the hole-transporting region comprises a charge-generating material.

15. An organic light-emitting device according to claim 14 wherein the charge-generating material is a p-dopant.

16. The organic light emitting device of claim 15, wherein the p-dopant is selected from the group consisting of quinone derivatives, metal oxides, and cyano-containing compounds.

17. An organic light-emitting device according to claim 11 wherein the electron-transporting region comprises a metal complex.

18. The organic light emitting device of claim 11, wherein the electron transport region comprises a Li complex.

19. The organic light emitting device of claim 11, wherein the electron transport region comprises ET-D1 or ET-D2:

20. a display apparatus comprising the organic light emitting device according to claim 9, wherein a first electrode of the organic light emitting device is electrically coupled to a source electrode and a drain electrode of a thin film transistor.